Ketone and process of producing same.



UNITED STATES v PATENT OFFICE.

ALEX B. DAVIS, OF INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI LILLY AND COMPANY, OF INDIANAPOLIS, INDIANA, A CORPORATION OF INDIANA,

KETONE AND PROCESS OF PRODUCING SAME.

No Drawing.

Specification of Letters Patent.

Application filed July 14, 1913. Serial No. 778,884.

Patented Oct. 27, 1914.

To all whom it may concern Be it known that I, ALEX B. DAVIS, a citizen of the United States, residing at Indianapolis, Marion county, and State of Indiana, have invented and discovered certain new and useful Improvements in Ketones and Processes of Producing Same, of which the following is a specification.

The invention relates to a new ketone derived from chlor methyl omega brom propyl-carbinol by oxidation, which may be called chlor-methyl-omega-brom-propyl-ketone. It is a valuable intermediate product in the preparation of other compounds.

To repare the ketone, chlor-methylomega-brom-propyl-carbinol, which is produced by the condensation of bromethylmagnesium-bromid. and epichlorhydrin, is added to sufficient potassium dichromate to burn off two atoms of hydrogen when sulfuric acid is added to the mixture in suflicient quantity to combine with all the potassium.

The process in detail may be carried out as follows: 157 parts by weight of chlormethyl omega brom propyl carbinol which may be ascribed the following formula:

Much heat is evolved during the reaction and the temperature should not be allowed to exceed 50 as other by-products will be formed. When all the acid has been added the temperature is held at 50 or nearly so until all of the dichromate has dissolved. The flask is now heated for an hour on the water bath and then distilled with steam. The ketone is readily volatile with steam and passes over readil When the distillate no longer has the s arp irritant odor of the ketone, the distillation is stopped, the total distillate extracted with ether as many times as necessary; the ether is evaporated and the residue distilled in vacuum when it boils at 941 C. under 20 m. no. pressure.

What I claim is:

1. A ketone of the formula:

2. The process of producing a ketone by oxidizing a carbinol of the formula- 3. The process of producing a ketone by condensing bromethyl magnesium bromid and epichlorhydrin and subjecting the resulting carbinol to oxidation.

4:. The process of producing a ketone which consists in condensing bromethylmagnesium-bromid and epichlorhydrin, adding sufficient potassium dichromate to burn off two atoms of hydrogen and then adding suflicient sulfuric acid to combine with all the potassium.

5. The process of producing a ketone consisting in adding potassium dichromate to chlormethyl omega brom-propyl carbinol and then adding an acid capable of combining with the potassium.

6. The process of adding to chlor-methylomega-brompropyl carbinol, a salt capable of burning off two atoms of hydrogen, then adding an acid suitable for combining with the positive element of the salt-and to effect oxidation, maintaining the temperature during reaction at not more than 50 and then distilling the compound.

7. The process of producing a ketone chromate to chlor methyl omega brom propyl-carbinol thennad'giing sulfuric acid this thirtieth day of June, A. D. nineteen while the mixture is 'mamtained at a comhundred and thirteen; pamtively low temperature, maintaining the temperature during reaction at not more 1 ALEX V 5 than 50 and distilling ofi' the ketone. Witnesses:

In witness whereof, I have hereunto set FRANK R. ELDRED,

my hand and seal at Indianapolis, Indiana, H. W. RHODEBAM'EL. 

